Acetic Acid → HCID 67068492, Verbindung

HRID 536110Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 536110
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([Br:12])[C:10]=1[NH2:11])=[O:5])[CH3:2].[CH:13](=O)[CH:14]([CH3:16])[CH3:15].[BH3-]C#N.[Na+].CC(O)=O.[OH-].[Na+]>C(Cl)Cl.CO>[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([Br:12])[C:10]=1[NH:11][CH2:13][CH:14]([CH3:16])[CH3:15])=[O:5])[CH3:2]

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 6561Isobutyraldehyde2×HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydride2×HCID 67068498Ethyl 3-amino-4-bromo-1H-pyrrole-2-carboxylate

Produkt 1

HCID 67068492HCID 67068492, VerbindungAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

3-Amino-4-bromo-1H-pyrrole-2-carboxylic acid ethyl ester (0.136 g, 0.58 mmol) and isobutyraldehyde (0.067 g, 0.93 mmol) were stirred in CH2Cl2/MeOH (1:1, 3 mL) at r.t. for 2 h. NaCNBH3 (0.065 g, 1.04 mmol) and HOAc (0.035 g, 0.58 mmol) were added and the mixture was stirred at r.t. for 2 h and then stirred at 50° C. for 16 h. Additional isobutyraldehyde (1 equiv.) and NaCNBH3 (0.5 equiv.) were added and the mixture was continued stirring at 50° C. overnight. The reaction mixture was neutralized with 2 M NaOH solution and the solvents were removed in vacuo. The residue was taken up in ethyl acetate and extracted with water. The organic layer was dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (heptane/ethyl acetate gradient, 0 to 30% ethyl acetate), obtaining the title compound (0.040 g, 24%) as a white solid.

Aufarbeitung

  1. stirringstirred at 50° C. for 16 h
  2. stirringthe mixture was continued stirring at 50° C. overnight
  3. customthe solvents were removed in vacuo
  4. extractionextracted with water
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (heptane/ethyl acetate gradient, 0 to 30% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-2d9b3c421cbe44938460dbd1e202c417
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859568B2

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